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MOSCOW — Apple and Google removed an app aimed at coordinating a protest vote from the country on Friday in this weekend’s Russian elections, a blow to opponents of President Vladimir V. Putin and a display of Silicon Valley’s limits when it comes to resisting crackdowns on business worldwide.

The decisions come after Russian officials who claimed the app is illegal have threatened to prosecute local employees of Apple and Google – a sharp escalation in the Kremlin’s campaign to rein in the country’s largely uncensored internet. A person familiar with Google’s decision said authorities named specific people who would face prosecution and asked him to remove the app.

The person refused to reveal his identity for fear of angering the Russian government. Google has more than 100 employees in the country.

Apple did not respond to phone calls, emails or text messages asking for comment.

The app was created and promoted by allies of opposition leader Aleksei A. Navalny, who hope to use it to consolidate opposition votes in each of Russia’s 225 constituencies. It disappeared from the two tech platforms as the voting continued. three-day parliamentary elections, which Mr. Putin’s United Russia party — in a carefully managed system – has the advantage of command.

Mr. Navalny’s team reacted angrily to the decision, arguing that the companies made a damaging concession to the Russians. “Removing the Navalny app from stores is a shameful act of political censorship,” said Ivan Zhdanov, Mr. Navalny’s deputy. said on Twitter. “Russia’s authoritarian government and propaganda will get excited.”

The resolutions also drew harsh condemnation from free speech activists in the West. “Russian pressure can explain, but it does not relieve companies of responsibility” David KayeA former United Nations official responsible for investigating freedom of expression issues said on Twitter. “They are de facto complicit as they have put themselves in this position for years by complying with Russian law in order to take part in this market.”

The extraordinary pressure on Google and Apple is indicative of the threat the Kremlin sees in Mr Navalny’s “smart vote” effort and the growing role technology plays as a tool of political power. United Russia’s approval ratings in state-run polls dropped to 30 percent, compared to 40 percent before the last parliamentary elections in 2016. Consolidation of opposition votes can beat the United Russia candidates in competitive regions, as it is only necessary to win a simple majority.

Putin’s spokesman, Dmitri S. Peskov, in a regular meeting with journalists on Friday, argued that the practice is illegal in Russia; Mr. Navalny’s move outlawed as extremist this summer. “Both platforms have been informed and it appears that they have taken these decisions in accordance with the law,” he said.

Maintaining open, uncensored access to their services, especially in authoritarian countries, is becoming one of the most vexing challenges for American tech companies like Apple, Google, Facebook and Twitter. Authorities in countries like India, Myanmar and Turkey are increasingly pressing companies to censor certain political speech or order internet blackouts to block access to the internet.

NGOs warned forcing companies to comply The combination of laws and regulations risks creating a more fragmented internet where access to information and products will depend on where people are. Companies must weigh the value of offering their services in a country like Russia, where they are seen as more independent from local technology platforms, as Google does in China, against the cost of leaving altogether.

The pressure to block certain content from Silicon Valley on their platforms doesn’t just come from more authoritarian governments. Policymakers in the United States and Europe are asking companies to do more to address hate speech, misinformation and other toxic content. Republicans in the United States argue that they are censored online.

In Russia, national internet regulator Roskomnadzor has repeatedly requested companies to remove certain content due to fines or restrictions on access to their products. The government says American internet companies are interfering in Russia’s internal affairs by allowing anti-Kremlin activists to freely use their platforms.

The Russian government has been increasingly outspoken in recent days about its willingness to use threats of arrest to thwart use of the app. “With the involvement of Apple and Google, certain crimes are committed, the scale of which may only increase in the coming days,” Vladimir Dzhabarov, a member of Russia’s upper house of Parliament, said on Thursday. “Persons who contribute to the avoidance of liability of their parent company on the territory of the Russian Federation will be punished.”

We’ll see if Apple and Google’s concession on Friday turns into a turning point in how strongly American tech giants are willing to resist Kremlin pressure. Amid Russia’s crackdown on the opposition this year, the most popular Silicon Valley platforms remained freely accessible, allowing journalists and activists to continue to deliver their messages. On YouTube, for example, the Navalny team’s investigations into corruption in the Russian elite regularly receive millions of views.

But Friday’s move could encourage governments in the Kremlin, as well as elsewhere in the world, to use the threat of prosecuting employees to gain leverage against companies. It offers a test of Silicon Valley ideals around free expression and the open internet, balanced not only against profit but also against the safety of its employees.

Removal of Facebook and Twitter posts, YouTube videos, and other internet content happens on a fairly regular basis as companies worldwide try to comply with local laws. Apple has removed apps in China that offend government censors, including software that would allow Chinese users to access the open global internet. 2016 court decision in Russia led Apple and Google to remove LinkedIn From app stores when LinkedIn doesn’t comply with a law that requires data about Russian users to be stored within country borders.

But Natalia Krapiva, legal counsel for Access Now, a nonprofit group that monitors internet censorship, said the removals by Google and Apple on Friday set little precedent given the election risks and Mr. . “This is really a new phenomenon to go after app stores,” said Ms. Krapiva.

While companies prefer to be seen as neutral platforms, Ms. Krapiva said industry leaders should speak out more strongly to defend freedom of expression and the open internet, especially if company employees are threatened with criminal prosecution.

Otherwise, “it looks like they’re standing on the side of the government,” said Ms. Krapiva.

Although events are rarely made public, governments have used the possibility of prosecution in the past. In 2016, a Facebook executive was arrested in Brazil after the company refused to hand over WhatsApp data related to a drug trafficking investigation. authorities in India and Thailand also among those who have threatened jail putting pressure on social media companies.

Russian officials have been pressuring Apple and Google for weeks to remove the Navalny team’s voting practice. When Mr. Navalny’s websites were blocked inside Russia, the practice became a loophole that allowed the jailed politician’s exiled allies to continue to reach a large audience. Nearly every smartphone runs Apple’s iOS or Google’s Android operating system, making app stores the main artery for getting any product to the public.

The Russian Foreign Ministry summoned the US ambassador to Moscow, John J. Sullivan, last week, and announced that “American ‘digital giants'” were breaking Russian law “in the context of the preparation and conduct of elections.”

Enforcement officers visited Google’s offices earlier this week to enforce court-ordered measures against the protest voting campaign, state media reported.

The Navalny app continued to work on Apple and Android phones for those who had already downloaded the software.

The app is at the center of the opposition leader’s protest strategy, which he calls “smart voting.” The goal is to defeat as many candidates as possible representing the ruling United Russia party by getting all opposition-minded voters in each region to choose the same opponent, whether they agree or not.

The “Navalny” application coordinates the process by requesting a user’s address and responding with the name of the candidate who should vote.

On Friday, the Navalny team tried to get the names of “smart ballot” elections through other methods, such as automatic replies on messaging app Telegram. But they have expressed their anger at Apple and Google for what they see as enduring Kremlin pressure.

“This shameful day will long remain in history,” Leonid Volkov, Mr. Navalny’s long-time chief of staff, wrote on his Telegram account.

Anton Troianovski Reported from Moscow and Adam Satariano from London. Oleg Matsnev and Ivan Nechepurenko Contributed to reporting from Moscow.